RU2345981C2 - ЦИКЛОАЛКИЛИДЕНОВЫЕ СОЕДИНЕНИЯ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ НА ИХ ОСНОВЕ, ИХ ПРИМЕНЕНИЕ И СПОСОБ СЕЛЕКТИВНОГО СВЯЗЫВАНИЯ ERα- И ERβ-ЭСТРОГЕНОВЫХ РЕЦЕПТОРОВ - Google Patents
ЦИКЛОАЛКИЛИДЕНОВЫЕ СОЕДИНЕНИЯ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ НА ИХ ОСНОВЕ, ИХ ПРИМЕНЕНИЕ И СПОСОБ СЕЛЕКТИВНОГО СВЯЗЫВАНИЯ ERα- И ERβ-ЭСТРОГЕНОВЫХ РЕЦЕПТОРОВ Download PDFInfo
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- RU2345981C2 RU2345981C2 RU2006101632/04A RU2006101632A RU2345981C2 RU 2345981 C2 RU2345981 C2 RU 2345981C2 RU 2006101632/04 A RU2006101632/04 A RU 2006101632/04A RU 2006101632 A RU2006101632 A RU 2006101632A RU 2345981 C2 RU2345981 C2 RU 2345981C2
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- Russia
- Prior art keywords
- methyl
- phenyl
- hydroxyphenyl
- tetramethylcyclohexylidene
- acid
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- 150000001875 compounds Chemical class 0.000 title claims abstract 34
- 238000000034 method Methods 0.000 title claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 3
- 239000000262 estrogen Substances 0.000 title abstract 3
- 102100029951 Estrogen receptor beta Human genes 0.000 title 1
- 101001010910 Homo sapiens Estrogen receptor beta Proteins 0.000 title 1
- 102000005962 receptors Human genes 0.000 title 1
- 108020003175 receptors Proteins 0.000 title 1
- 150000001408 amides Chemical class 0.000 claims abstract 4
- 150000002148 esters Chemical class 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 230000000694 effects Effects 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- -1 2-fluoro-4-hydroxyphenyl Chemical group 0.000 claims 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 229910052760 oxygen Chemical group 0.000 claims 4
- 239000001301 oxygen Chemical group 0.000 claims 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 210000000988 bone and bone Anatomy 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 208000004746 Atrophic Vaginitis Diseases 0.000 claims 2
- 206010003693 Atrophic vulvovaginitis Diseases 0.000 claims 2
- 206010003694 Atrophy Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010054089 Depressive symptom Diseases 0.000 claims 2
- 201000009273 Endometriosis Diseases 0.000 claims 2
- 206010057671 Female sexual dysfunction Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 230000037444 atrophy Effects 0.000 claims 2
- 238000005115 demineralization Methods 0.000 claims 2
- 230000002328 demineralizing effect Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 201000010808 postmenopausal atrophic vaginitis Diseases 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- IIGBAYDKIWBPCU-AIHHMALZSA-N (2s)-1-[(e)-3-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)\C=C\C1=CC=C(C(C=2C=CC(O)=CC=2)=C2CCCCCC2)C=C1 IIGBAYDKIWBPCU-AIHHMALZSA-N 0.000 claims 1
- NDEYJKKJWBKIIR-CAOOACKPSA-N (e)-3-[3-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(=CC=1)C=1C=C(\C=C\C(O)=O)C=CC=1)C1=CC=C(O)C=C1 NDEYJKKJWBKIIR-CAOOACKPSA-N 0.000 claims 1
- PDQBWIBKUHIICJ-NTUHNPAUSA-N (e)-3-[3-chloro-4-[cyclohexylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound ClC1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCC1 PDQBWIBKUHIICJ-NTUHNPAUSA-N 0.000 claims 1
- MQANJDKHDUDLHH-KPKJPENVSA-N (e)-3-[4-[(3-chloro-4-hydroxyphenyl)-(2,2,6,6-tetramethyloxan-4-ylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)OC(C)(C)CC1=C(C=1C=C(Cl)C(O)=CC=1)C1=CC=C(\C=C\C(O)=O)C=C1 MQANJDKHDUDLHH-KPKJPENVSA-N 0.000 claims 1
- IEEOYDJCAZMNFY-KPKJPENVSA-N (e)-3-[4-[(3-chloro-4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=C(Cl)C(O)=CC=1)C1=CC=C(\C=C\C(O)=O)C=C1 IEEOYDJCAZMNFY-KPKJPENVSA-N 0.000 claims 1
- IFKHGIYQTGYJSS-NTEUORMPSA-N (e)-3-[4-[(3-chloro-4-hydroxyphenyl)-cycloheptylidenemethyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=C(Cl)C(O)=CC=1)=C1CCCCCC1 IFKHGIYQTGYJSS-NTEUORMPSA-N 0.000 claims 1
- XLKZMOCPFOKRCN-MDWZMJQESA-N (e)-3-[4-[(3-chloro-4-hydroxyphenyl)-cyclohexylidenemethyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=C(Cl)C(O)=CC=1)=C1CCCCC1 XLKZMOCPFOKRCN-MDWZMJQESA-N 0.000 claims 1
- MRIRQIZLHFUDJT-KPKJPENVSA-N (e)-3-[4-[(3-fluoro-4-hydroxyphenyl)-(2,2,6,6-tetramethyloxan-4-ylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)OC(C)(C)CC1=C(C=1C=C(F)C(O)=CC=1)C1=CC=C(\C=C\C(O)=O)C=C1 MRIRQIZLHFUDJT-KPKJPENVSA-N 0.000 claims 1
- OMGMXYACDPFCEG-KPKJPENVSA-N (e)-3-[4-[(3-fluoro-4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=C(F)C(O)=CC=1)C1=CC=C(\C=C\C(O)=O)C=C1 OMGMXYACDPFCEG-KPKJPENVSA-N 0.000 claims 1
- OLJWDJBIESYNEY-LFYBBSHMSA-N (e)-3-[4-[(4,4-dimethylcyclohexylidene)-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1CC(C)(C)CCC1=C(C=1C=CC(\C=C\C(O)=O)=CC=1)C1=CC=C(O)C=C1 OLJWDJBIESYNEY-LFYBBSHMSA-N 0.000 claims 1
- QZDDNGHVOZKCHV-SAPNQHFASA-N (e)-3-[4-[(4-hydroxyphenyl)-(2,2,6,6-tetramethyloxan-4-ylidene)methyl]phenyl]-2-methylprop-2-enoic acid Chemical compound C1=CC(\C=C(/C)C(O)=O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CC(C)(C)OC(C)(C)C1 QZDDNGHVOZKCHV-SAPNQHFASA-N 0.000 claims 1
- LNBGFCKFUBABPV-VGOFMYFVSA-N (e)-3-[4-[(4-hydroxyphenyl)-(2,2,6,6-tetramethyloxan-4-ylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)OC(C)(C)CC1=C(C=1C=CC(\C=C\C(O)=O)=CC=1)C1=CC=C(O)C=C1 LNBGFCKFUBABPV-VGOFMYFVSA-N 0.000 claims 1
- NNFCEKYJMMYGOD-VGOFMYFVSA-N (e)-3-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]prop-2-enamide Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(\C=C\C(N)=O)=CC=1)C1=CC=C(O)C=C1 NNFCEKYJMMYGOD-VGOFMYFVSA-N 0.000 claims 1
- LBVZZPZACRTCIB-VGOFMYFVSA-N (e)-3-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(\C=C\C(O)=O)=CC=1)C1=CC=C(O)C=C1 LBVZZPZACRTCIB-VGOFMYFVSA-N 0.000 claims 1
- OSQPSKQSEZRPPY-CCEZHUSRSA-N (e)-3-[4-[(4-hydroxyphenyl)-(oxan-4-ylidene)methyl]phenyl]-2-methylprop-2-enoic acid Chemical compound C1=CC(\C=C(/C)C(O)=O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCOCC1 OSQPSKQSEZRPPY-CCEZHUSRSA-N 0.000 claims 1
- NQIFKFNBTBROPX-XCVCLJGOSA-N (e)-3-[4-[(4-hydroxyphenyl)-(oxan-4-ylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCOCC1 NQIFKFNBTBROPX-XCVCLJGOSA-N 0.000 claims 1
- OLUZJHMLWRCIRT-XCVCLJGOSA-N (e)-3-[4-[(4-hydroxyphenyl)-(thian-4-ylidene)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCSCC1 OLUZJHMLWRCIRT-XCVCLJGOSA-N 0.000 claims 1
- GWKQRNXTGAHPBR-GINUTJKVSA-N (e)-3-[4-[9-bicyclo[3.3.1]nonanylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1C2CCCC1CCC2 GWKQRNXTGAHPBR-GINUTJKVSA-N 0.000 claims 1
- KNLYVVNUKJDQLW-NTEUORMPSA-N (e)-3-[4-[cycloheptylidene-(3-fluoro-4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=C(F)C(O)=CC=1)=C1CCCCCC1 KNLYVVNUKJDQLW-NTEUORMPSA-N 0.000 claims 1
- SGYCOKAIMUWWHK-SDNWHVSQSA-N (e)-3-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]-2-fluorophenyl]prop-2-enoic acid Chemical compound C1=C(F)C(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCCC1 SGYCOKAIMUWWHK-SDNWHVSQSA-N 0.000 claims 1
- YEZMYWLJHQMEKH-CXUHLZMHSA-N (e)-3-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enamide Chemical compound C1=CC(/C=C/C(=O)N)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCCC1 YEZMYWLJHQMEKH-CXUHLZMHSA-N 0.000 claims 1
- FIXMRJCBRFHJKY-CXUHLZMHSA-N (e)-3-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCCC1 FIXMRJCBRFHJKY-CXUHLZMHSA-N 0.000 claims 1
- VUFJYXGYPUYTEQ-MDWZMJQESA-N (e)-3-[4-[cyclohexylidene-(2,3-difluoro-4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C(=C(F)C(O)=CC=1)F)=C1CCCCC1 VUFJYXGYPUYTEQ-MDWZMJQESA-N 0.000 claims 1
- MUSXRSKAGXTKQI-MDWZMJQESA-N (e)-3-[4-[cyclohexylidene-(3-fluoro-4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=C(F)C(O)=CC=1)=C1CCCCC1 MUSXRSKAGXTKQI-MDWZMJQESA-N 0.000 claims 1
- KKMNIGGQSHOGSX-XNTDXEJSSA-N (e)-3-[4-[cyclohexylidene-(4-hydroxy-2,3-dimethylphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound CC1=C(O)C=CC(C(=C2CCCCC2)C=2C=CC(\C=C\C(O)=O)=CC=2)=C1C KKMNIGGQSHOGSX-XNTDXEJSSA-N 0.000 claims 1
- JMEZCGIITJETTP-NTEUORMPSA-N (e)-3-[4-[cyclohexylidene-(4-hydroxy-2-methylphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound CC1=CC(O)=CC=C1C(C=1C=CC(\C=C\C(O)=O)=CC=1)=C1CCCCC1 JMEZCGIITJETTP-NTEUORMPSA-N 0.000 claims 1
- MFVFAHVLQFEBJH-NTEUORMPSA-N (e)-3-[4-[cyclohexylidene-(4-hydroxy-3-methylphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=C(O)C(C)=CC(C(=C2CCCCC2)C=2C=CC(\C=C\C(O)=O)=CC=2)=C1 MFVFAHVLQFEBJH-NTEUORMPSA-N 0.000 claims 1
- YVVYTWWQCLGBSD-JLHYYAGUSA-N (e)-3-[4-[cyclohexylidene-(4-hydroxyphenyl)methyl]-2-fluorophenyl]prop-2-enoic acid Chemical compound C1=C(F)C(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCC1 YVVYTWWQCLGBSD-JLHYYAGUSA-N 0.000 claims 1
- ACHILXBCZRXRSO-SDNWHVSQSA-N (e)-3-[4-[cyclohexylidene-(4-hydroxyphenyl)methyl]-2-methylphenyl]prop-2-enoic acid Chemical compound C1=C(\C=C\C(O)=O)C(C)=CC(C(=C2CCCCC2)C=2C=CC(O)=CC=2)=C1 ACHILXBCZRXRSO-SDNWHVSQSA-N 0.000 claims 1
- VLPXUKHZHBUJFJ-NTUHNPAUSA-N (e)-3-[4-[cyclohexylidene-(4-hydroxyphenyl)methyl]-3-fluorophenyl]prop-2-enoic acid Chemical compound FC1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCC1 VLPXUKHZHBUJFJ-NTUHNPAUSA-N 0.000 claims 1
- GBGHTHKZJPQDEL-OVCLIPMQSA-N (e)-3-[4-[cyclohexylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enamide Chemical compound C1=CC(/C=C/C(=O)N)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCC1 GBGHTHKZJPQDEL-OVCLIPMQSA-N 0.000 claims 1
- GOPACCJWLSLIKG-OVCLIPMQSA-N (e)-3-[4-[cyclohexylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCC1 GOPACCJWLSLIKG-OVCLIPMQSA-N 0.000 claims 1
- KCKMNQWYQVMVAR-LICLKQGHSA-N (e)-3-[4-[cyclooctylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCCCC1 KCKMNQWYQVMVAR-LICLKQGHSA-N 0.000 claims 1
- MVKWPMBMEANCLC-VGOFMYFVSA-N (e)-3-[4-[cyclopentylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C/C(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCC1 MVKWPMBMEANCLC-VGOFMYFVSA-N 0.000 claims 1
- LHUATOCBPYWODS-WOJGMQOQSA-N 1-[(e)-3-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoyl]piperidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CCCN1C(=O)\C=C\C1=CC=C(C(C=2C=CC(O)=CC=2)=C2CCCCCC2)C=C1 LHUATOCBPYWODS-WOJGMQOQSA-N 0.000 claims 1
- PAPPTBRXLMZUQW-CXUHLZMHSA-N 1-[(e)-3-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]phenyl]prop-2-enoyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(=O)\C=C\C1=CC=C(C(C=2C=CC(O)=CC=2)=C2CCCCCC2)C=C1 PAPPTBRXLMZUQW-CXUHLZMHSA-N 0.000 claims 1
- XYCIIMWSQYRCQR-UHFFFAOYSA-N 1-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C(C=1C=CC(O)=CC=1)=C1CC(C)(C)CC(C)(C)C1 XYCIIMWSQYRCQR-UHFFFAOYSA-N 0.000 claims 1
- LYOSNVJOHSWGKF-UHFFFAOYSA-N 2-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CC(C)(C)CC(C)(C)C1 LYOSNVJOHSWGKF-UHFFFAOYSA-N 0.000 claims 1
- AUJKPDOYKWKHRS-UHFFFAOYSA-N 2-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenoxy]acetonitrile Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(OCC#N)=CC=1)C1=CC=C(O)C=C1 AUJKPDOYKWKHRS-UHFFFAOYSA-N 0.000 claims 1
- AVBTULZSRANEOV-UHFFFAOYSA-N 2-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]acetic acid Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(CC(O)=O)=CC=1)C1=CC=C(O)C=C1 AVBTULZSRANEOV-UHFFFAOYSA-N 0.000 claims 1
- HDKKZKFDXRMNFK-UHFFFAOYSA-N 2-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]benzoic acid Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(=CC=1)C=1C(=CC=CC=1)C(O)=O)C1=CC=C(O)C=C1 HDKKZKFDXRMNFK-UHFFFAOYSA-N 0.000 claims 1
- GPLATJSRUMTQNL-UHFFFAOYSA-N 2-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCCC1 GPLATJSRUMTQNL-UHFFFAOYSA-N 0.000 claims 1
- XSLDHJNGYVYIKF-UHFFFAOYSA-N 2-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCCC1 XSLDHJNGYVYIKF-UHFFFAOYSA-N 0.000 claims 1
- YWJICDGEDGTZPW-UHFFFAOYSA-N 2-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]phenoxy]acetonitrile Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(OCC#N)=CC=1)=C1CCCCCC1 YWJICDGEDGTZPW-UHFFFAOYSA-N 0.000 claims 1
- BIWQNDCURCNWFY-UHFFFAOYSA-N 2-fluoro-4-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]benzonitrile Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(=CC=1)C=1C=C(F)C(C#N)=CC=1)C1=CC=C(O)C=C1 BIWQNDCURCNWFY-UHFFFAOYSA-N 0.000 claims 1
- JGAPYXCUYNDKRK-UHFFFAOYSA-N 3-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]benzamide Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(=CC=1)C=1C=C(C=CC=1)C(N)=O)C1=CC=C(O)C=C1 JGAPYXCUYNDKRK-UHFFFAOYSA-N 0.000 claims 1
- XHMUAVPRJQCENI-UHFFFAOYSA-N 3-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]benzoic acid Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(=CC=1)C=1C=C(C=CC=1)C(O)=O)C1=CC=C(O)C=C1 XHMUAVPRJQCENI-UHFFFAOYSA-N 0.000 claims 1
- FDMCHUIWHLKNDZ-UHFFFAOYSA-N 3-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]propanoic acid Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(CCC(O)=O)=CC=1)C1=CC=C(O)C=C1 FDMCHUIWHLKNDZ-UHFFFAOYSA-N 0.000 claims 1
- AXSLABKKPZBWOT-UHFFFAOYSA-N 3-[4-[cycloheptylidene-(4-hydroxyphenyl)methyl]-3-fluorophenyl]prop-2-enoic acid Chemical compound FC1=CC(C=CC(=O)O)=CC=C1C(C=1C=CC(O)=CC=1)=C1CCCCCC1 AXSLABKKPZBWOT-UHFFFAOYSA-N 0.000 claims 1
- KWOWYVUSZAURIL-UHFFFAOYSA-N 4-[(4,4-dimethylcyclohexylidene)-(4-hydroxyphenyl)methyl]benzoic acid Chemical compound C1CC(C)(C)CCC1=C(C=1C=CC(=CC=1)C(O)=O)C1=CC=C(O)C=C1 KWOWYVUSZAURIL-UHFFFAOYSA-N 0.000 claims 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
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- 206010047791 Vulvovaginal dryness Diseases 0.000 claims 1
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- 125000004429 atom Chemical group 0.000 claims 1
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- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
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- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
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- 229940126601 medicinal product Drugs 0.000 claims 1
- GIXNKLDQTOGANE-UHFFFAOYSA-N n-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(C=1C=CC(O)=CC=1)=C1CC(C)(C)CC(C)(C)C1 GIXNKLDQTOGANE-UHFFFAOYSA-N 0.000 claims 1
- XQJWAVQFRPTEQX-UHFFFAOYSA-N n-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]benzenesulfonamide Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(NS(=O)(=O)C=2C=CC=CC=2)=CC=1)C1=CC=C(O)C=C1 XQJWAVQFRPTEQX-UHFFFAOYSA-N 0.000 claims 1
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- DDYXJHBDEXURAL-UHFFFAOYSA-N n-[4-[4-[(4-hydroxyphenyl)-(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl]phenyl]methanesulfonamide Chemical compound C1C(C)(C)CC(C)(C)CC1=C(C=1C=CC(=CC=1)C=1C=CC(NS(C)(=O)=O)=CC=1)C1=CC=C(O)C=C1 DDYXJHBDEXURAL-UHFFFAOYSA-N 0.000 claims 1
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- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 208000012201 sexual and gender identity disease Diseases 0.000 claims 1
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- 230000001457 vasomotor Effects 0.000 claims 1
- 229940011871 estrogen Drugs 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 0 C[C@@](C(*)(*)*C(*)(*)C1*)C1=C(C1=C*(C)C=C(*)C=C1)C1=CC=C(*)C(C)(C)C=C1 Chemical compound C[C@@](C(*)(*)*C(*)(*)C1*)C1=C(C1=C*(C)C=C(*)C=C1)C1=CC=C(*)C(C)(C)C=C1 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
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RU2525397C2 (ru) * | 2012-09-10 | 2014-08-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Пермский государственный национальный исследовательский университет" | 1-(4-этилфенил)-2-[3-(4-этилфенил)-2-(1н)-хиноксалинилиден]-1-этанон, обладающий анальгетической активностью |
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US7723393B2 (en) * | 2005-05-25 | 2010-05-25 | Glaxosmithkline Llc | Cycloalkylidene compounds as selective estrogen receptor modulators |
US20060281788A1 (en) | 2005-06-10 | 2006-12-14 | Baumann Christian A | Synergistic modulation of flt3 kinase using a flt3 inhibitor and a farnesyl transferase inhibitor |
JP2009516696A (ja) * | 2005-11-22 | 2009-04-23 | スミスクライン ビーチャム コーポレーション | 化学化合物 |
BRPI0710548B8 (pt) | 2006-04-20 | 2021-05-25 | Janssen Pharmaceutica Nv | inibidores de c-fms cinase, composição farmacêutica e forma de dosagem farmacêutica |
US8697716B2 (en) | 2006-04-20 | 2014-04-15 | Janssen Pharmaceutica Nv | Method of inhibiting C-KIT kinase |
AU2007240437B2 (en) | 2006-04-20 | 2012-12-06 | Janssen Pharmaceutica N.V. | Heterocyclic compounds as inhibitors of c-fms kinase |
WO2008030771A1 (en) * | 2006-09-08 | 2008-03-13 | Smithkline Beecham Corporation | Cyclic alkylidene compounds as selective estrogen receptor modulators |
JO3240B1 (ar) | 2007-10-17 | 2018-03-08 | Janssen Pharmaceutica Nv | c-fms مثبطات كيناز |
CN102786394B (zh) * | 2012-07-30 | 2017-03-01 | 中国医学科学院医药生物技术研究所 | 取代双芳基亚甲基环烷基衍生物及其制备方法和应用 |
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ES2654161T3 (es) * | 2013-05-28 | 2018-02-12 | Astrazeneca Ab | Compuestos químicos |
WO2015026990A2 (en) | 2013-08-20 | 2015-02-26 | University Of Washington Through Its Center For Commercialization | Novel and specific inhibitors of cytochrome p450 26 retinoic acid hydrolase |
EP3307747A4 (en) | 2015-06-12 | 2019-02-27 | Simon Fraser University | AMIDE-LINKED EP4-BISPHOSPHONATE AGONIST COMPOUNDS AND USES THEREOF |
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GB971908A (en) * | 1960-11-22 | 1964-10-07 | Ferrosan Ab | Dihydroxybenzhydrylidene cycloalkanes and derivatives thereof |
US3760007A (en) | 1970-06-11 | 1973-09-18 | Schering Corp | Bicyclic benzhydrylidene derivatives |
US3936493A (en) | 1973-04-17 | 1976-02-03 | Ortho Pharmaceutical Corporation | Diarylmethylenes |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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RU2525397C2 (ru) * | 2012-09-10 | 2014-08-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Пермский государственный национальный исследовательский университет" | 1-(4-этилфенил)-2-[3-(4-этилфенил)-2-(1н)-хиноксалинилиден]-1-этанон, обладающий анальгетической активностью |
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JP2007500705A (ja) | 2007-01-18 |
AU2004261627C1 (en) | 2009-02-05 |
WO2005012220A3 (en) | 2005-03-24 |
WO2005012220A9 (en) | 2005-05-19 |
RU2006101632A (ru) | 2006-09-10 |
WO2005012220A2 (en) | 2005-02-10 |
BRPI0413013A (pt) | 2006-10-03 |
CA2533812C (en) | 2012-12-18 |
JP5013593B2 (ja) | 2012-08-29 |
CA2533812A1 (en) | 2005-02-10 |
US7799828B2 (en) | 2010-09-21 |
AU2004261627B2 (en) | 2008-06-12 |
AU2004261627A1 (en) | 2005-02-10 |
MA28015A1 (fr) | 2006-07-03 |
IL173192A0 (en) | 2006-06-11 |
ZA200600819B (en) | 2007-04-25 |
US7560589B2 (en) | 2009-07-14 |
NO20060403L (no) | 2006-02-06 |
US20070155839A1 (en) | 2007-07-05 |
NZ545032A (en) | 2009-02-28 |
CN1856461A (zh) | 2006-11-01 |
EP1667955A2 (en) | 2006-06-14 |
US20070213348A1 (en) | 2007-09-13 |
MXPA06001094A (es) | 2006-04-11 |
US7569601B2 (en) | 2009-08-04 |
US20090253659A1 (en) | 2009-10-08 |
KR20060066070A (ko) | 2006-06-15 |
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